Donald Trump is in court this week in New York City, again, for a multimillion dollar civil fraud trial. He, his sons, and the Trump organization have been accused of using false financial statements and inflating their net worth by billions. In addition to this case, Trump is facing four criminal indictments: the January 6th insurrection case in DC, the Stormy Daniels hush money case in New York, the classified documents case in Florida, and the political interference case in Georgia. It’s a lot to keep track of, but this civil trial is worth one's attention. If NY State Attorney General Letitia James succeeds, Trump could lose control of his businesses and his most valuable assets, like Trump Tower — along with whatever’s left of the public image he spent decades constructing on television and in the press. Russ Buettner is a reporter on the New York Times Investigation Desk, the team that hunted down Trump’s tax returns and other elusive financial documents, in an effort to understand how exactly the former president got his money and how he lost so much of it. For the midweek podcast, OTM correspondent Micah Loewinger called Russ to learn about what Trump’s history of fraud means for his future, the revelations of the trial so far, and what details have gotten lost in the deluge of coverage.

In this first episode of our new miniseries, We Don't Talk About Leonard, ProPublica reporters Andrea Bernstein, Andy Kroll, and Ilya Marritz investigate the background of the man who has played a critical role in the conservative takeover of America's courts — Leonard Leo. From his humble roots in middle class New Jersey, to a mansion in Maine where last year he hosted a fabulous party on the eve of the Supreme Court decision to tank “Roe.” 1. The night before the Supreme Court overturned Roe v. Wade, Leonard Leo threw a lavish party at his house in Maine. Listen. 2. Leonard Leo's journey from a high-schooler with the nickname "Moneybags Kid" to a high-ranking member of the Federalist Society. Listen. 3. Leonard Leo and the Federalist Society turn their attention to the state supreme courts. Listen. This podcast was created in partnership with ProPublica, a nonprofit newsroom that investigates abuses of power. Sign up to receive their biggest stories as soon as they’re published.

In late August, Gannett, the country’s largest newspaper company, rolled out a new artificial intelligence service that promised to automate high school sports coverage across the country. And within a matter of days it had gone horribly wrong. People on Twitter quickly discovered that bizarre phrases like “close encounters of the athletic kind,” or how one team “took victory away” from another, had shown up on Gannett news sites in Florida, Indiana, Georgia, Ohio, Kentucky, and Tennessee. As Scott Simon explained on NPR, in some of these AI articles there were robotic place holders where there should’ve been a mascot’s name. Jay Allred is the CEO of Source Media Properties, which includes Richland Source, a local news organization in Ohio, and LedeAI, the company that built the technology that Gannett was using to automate its high school coverage. For the midweek podcast, OTM correspondent Micah Loewinger speaks with Jay about what went wrong, why he wanted to build this technology in the first place, and whether this disaster had shaken his belief in its potential.

Thousands of protesters descended on New York as the United Nations convened its Climate Summit. On this week’s On the Media, hear how Big Oil is being taken to court for lying to the public about fossil fuels. Plus, a look at a global network of think tanks that’s been vilifying climate activism for decades.  1. Rebecca Leber [@rebleber], senior climate reporter at Vox, on why some climate activists are turning to lawsuits to make change. Listen. 2. Amy Westervelt [@amywestervelt], host and producer of the podcast Drilled, on how a network of think tanks is shaping perceptions of peaceful climate activism as dangerous and extreme. Listen. 3. Leah Sottile [@Leah_Sottile], extremism reporter and the host of the podcast Burn Wild, on how eco-terrorism became security priority for the U.S. government. Listen.   Music:Il Casanova de Federico Fellini - Nino RotaPrelude 8: The Invisibles - John Zorn It’s Raining - Irma Thomas Middlesex Times - Donnie Darko - Michael Andrews Way Down in the Hole - Tom WaitsPuck - John ZornFinal Retribution -John Zorn

The House has opened a formal impeachment inquiry into President Biden. On this week’s On the Media, find out exactly what Republicans are looking for–and why they should’ve already found it. Plus, geriatric men are the likely presidential nominees. Is there such a thing as “too old” for the job? 1. Stephen Collinson [@StCollinson], CNN senior political reporter, on the impact of a baseless impeachment inquiry on the institution of Presidential impeachments. Listen. 2. James Fallows [@JamesFallows], writer of the “Breaking the News'' newsletter on Substack, and the former chief speechwriter for the Carter administration, on if the press is tackling the age question correctly. Listen.  3. Dr. Steven N. Austad [@StevenAustad], The University of Alabama at Birmingham’s Protective Life Endowed Chair in Healthy Aging Research, on what the science of aging can tell us about a potential Biden second term. Listen.  4. Naomi Klein [@NaomiAKlein], journalist and author of Doppelganger: A Trip into the Mirror World, on being confused for writer and conspiracist Naomi Wolf for much of her career, and her exploration of doppelgangers and the mirror world the other Naomi inhabits. Listen.  Music:72 Degrees and Sunny - Thomas NewmanEye Surgery - Thomas Newman Lost Night - Bill Frisell Young at Heart - Brad Mehldau TrioDisfarmer Little Girl - Bill FrissellPavane, Op. 50 - Gabriel Faure - Academy of St. Martin in the FieldsThe First Time Ever I saw Your Face - Bert Jansch